HCID 18448589, compound → 4-Aminochroman-7-carbonitrile

HRID 32052Notes

Reaction equation

HRID 32052 reaction equation
[N:1]([CH:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]#[N:15])=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5]1)=[N+]=[N-]>CCOC(C)=O>[NH2:1][CH:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]#[N:15])=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5]1

Participants

3

Reactant 1

HCID 18448589HCID 18448589, compound

Product 1

HCID 223499724-Aminochroman-7-carbonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Azido-7-cyanochroman (Step D) (4.3 g, 21 mmol) was dissolved in EtOAc (200 mL) and purged with N2. Pd/C (10%, 0.6 g) was added and the reaction was purged with N2. The reaction was purged with H2 and rapidly stirred under a H2 atmosphere until consumption of starting material was complete by TLC analysis (approximately 1 h). The reaction was purged with N2, and filtered through Celite®. The Celite®was washed with MeOH. The solution was concentrated in vacuo to provide a residue which was purified by column chromatography (silica, 3% MeOH in CH2Cl2 plus 0.5% NH4OH) to provide the title compound. TLC Rf=0.3 (5% MeOH in CH2Cl2 plus 0.5% Et3N.

Workup

  1. custompurged with N2
  2. additionPd/C (10%, 0.6 g) was added
  3. customthe reaction was purged with N2
  4. customThe reaction was purged with H2
  5. customwas complete by TLC analysis (approximately 1 h)
  6. customThe reaction was purged with N2
  7. filtrationfiltered through Celite®
  8. washThe Celite®was washed with MeOH
  9. concentrationThe solution was concentrated in vacuo
  10. customto provide a residue which
  11. customwas purified by column chromatography (silica, 3% MeOH in CH2Cl2 plus 0.5% NH4OH)

Sources & evidence

ORD record
ord-280bf96b7774425899d950ca0b165f4e
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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